We look at the youth movement in cigars, from the fifth generation of Quesadas, to the Perez-Carrillo children and the Levin young guns at Ashton.

The mysteries of the cigar business have long been passed down from generation to generation, typically from father to son, often when that son reaches his 40s or 50s. But there's a new movement in the cigar business where a new, far younger generation is coming into its own. Instead of making phone calls, they do text messages. While their fathers carried matchbooks, they live on Facebook. And you're more likely to find them wearing designer clothing than khaki pants and plaid work shirts.

At three prominent cigar companies, this next generation of cigar personalities—many of them female—is beginning to make their impact on the industry. And some have already created their own cigars.

The Quesadas — The Fifth Generation

The most dramatic youth movement in the cigar industry is happening in Santiago, Dominican Republic, inside the wood-paneled walls of Manufactura de Tabacos S.A., or Matasa. This 35-year-old company, the first to roll cigars in Santiago's original free trade zone, is operating more and more under the influence of five 20- and 30-somethings who 63-year-old factory owner Manuel (Manolo) Quesada collectively refers to as "the young ones." They also go by the term "the fifth generation," as they are the fifth generation of Quesadas to work in the tobacco business.

"The young ones," says Manuel Quesada with his typical deadpan humor, "are building the pillars for my monument."

Ranging in age from 24 to 33, the youngsters have injected new life into the company. They are led by Quesada's two daughters, Patricia, 33, and Raquel, 31, attractive blondes with generous smiles and Blackberrys that sometimes seem to be living extensions of their arms. Patricia, who calls herself "the spokesperson of the fifth generation," focuses on administration, while Raquel spends most of her time on the production floor. Manuel Quesada's niece, Esther Quesada, 32, runs the tobacco farm and the leaf warehouse. Nephew José Manuel Bermudez, 28, known as Blondie for the color of his slicked-back hair, designed the company's Casa Magna label. He runs the box factory with help from Hostos Fernandez Quesada, 24, a slim, bespectacled nephew who just graduated from college and has a knack for technology. The newest member of the next generation, nephew Terence Joseph Reilly, joined the group just this summer, bringing the total from that generation to six.

With a father and grandfather running a cigar factory, Patricia and Raquel have been around cigars all their lives. They visited Matasa from an early age as well as the tobacco fields run by their uncle. Patricia has worked for the company longer; she began in late 1997, starting "at the bottom," going through each department, even cleaning floors, before settling in administration and accounting. Raquel started in 2000 and soon showed a knack for blending a cigar, participating in the blending of the Matasa 30th Anniversary, the Fonseca Cubano Viso Fuerte and the Fonseca Cubano Limitado, where she has taken "top billing," on the box, says her father. "Raquel is the second in command in the factory," he says.

Raquel has even been known to do more than a few things without her father's consent, which inevitably leads to discovery, then a dreaded page over the Matasa public address system. Patricia mimics her father's voice, describing what happens: "'Raquel Quesada, extension 23.' When you hear that," she says, beaming, "go the other way." The girls also
reveal that their father's bushy salt-and-pepper mustache has a habit of going up when he's angry.

So what gets her in trouble? "She changes my blends," Manuel says with a laugh. He says that he selects a blend, instructs Raquel to have the factory make it, then when she brings him a finished cigar (naturally leaving his office posthaste) he notices the difference when he takes a puff. That's when he reaches for the P.A. Later, he usually realizes that the change is beneficial. "It's OK," he says, showing considerable fatherly pride in his little girl's knack for making a cigar.

There's just the hint of good-natured sibling rivalry between the sisters. "Patricia is the one who always got what she wanted from my
father," says Raquel, smiling. "I got everything from my mom." Patricia smiles as well. "I know when he says 'no' how to get a 'yes.'" Raquel calls her father "Quesada" at work, something Patricia cannot do—"I call him Papa," she says.

While there were some dispensations made because they are female ("I used to work summers, and my mom would call the factory and say 'Is she sweating? I don't want her to sweat,'" says Raquel) the women say their dad is demanding. "Even though we're girls, he still expects a lot," says Patricia, describing 12-hour days and 10 p.m. work calls.

The fifth generation wasn't supposed to be this deeply involved in Matasa, certainly not this soon. But in 2002, everything at the company changed forever.
The plane was a small Cessna, and it set out from Santiago on the morning of April 17, bound for Haiti. The weather turned, and contact with the plane was lost. The following day, the downed aircraft was spotted atop Mount Pelona, one of the tallest mountains in the Caribbean.

All four aboard the plane were lost: Manuel's brother, Alvaro Quesada; his son Alvaro Jr., Julio Fajardo and the pilot. Fajardo was Manuel Quesada's right-hand man at Matasa, and the heir apparent to the factory. Alvaro Jr., 24 at the time, was being trained to one day take his place.

"When we lost half of our staff in 2002, we all knew we would have to pull together, but at first we had five years not even thinking about it. We were on autopilot for about five years," says Patricia. "A year ago [the members of the fifth generation] started having meetings once a week, without my father. There, we talked about how the industry has changed."

The fifth generation took a hard look at stronger tobaccos, the type of thing that just wasn't used very much at Matasa. The result is in the company's newest cigar, the Quesada 35th Anniversary, which was
created collectively by the youngsters.

One day, the five called Manuel Quesada into a meeting room, and presented him with a tray of five cigars. They told him they were the blend choices for the 35th Anniversary. "I said, 'I thought I was doing that,'" says Quesada. He started smoking. They started tweaking. "And they were the ones doing the tweaking. It was very refreshing," he says, calling the moment both proud and scary. "It's a cigar that the fifth
generation decided to do on their own. Unfortunately," he says with a laugh, "I didn't have anything to do with it."
The cigar is a milestone, not only for the considerable involvement by the youthful members of the Quesada family, but for its name. While the Quesadas have rolled cigars in the Dominican Republic since 1974 (before any member of the fifth generation was born), this is the first time the family name has appeared on a brand.

The squared-off cigar is made with a combination of Nicaraguan, Dominican and Ecuadoran leaf, including a wrapper that is grown in Ecuador from Arapiraca seed, which is usually grown in Brazil. "It's
totally different—we have never used these tobaccos at Matasa before," says Raquel Quesada. Adds her father: "It's a radical departure from the blends that the old man has been doing."
The cigar was previewed at the Madison Avenue Davidoff store in New York City on June 29. All six members of the fifth generation lined up to present the cigar as Patricia took to the microphone. Manuel stood far to the right, separate from the group, letting his daughters, nephews and niece bask in the glow of their creation.

"Tobacco has been an essential part of our lives since the day we were born," Patricia said to the crowd. "The love for tobacco, and this industry, is something we all carry in our hearts, our souls, and even our senses, and that is what has kept us going, and will continue to keep us going for more generations to come."

In a private moment, the two sisters reflect on the journey the fifth generation at Matasa has taken, particularly the female contingent. "I think a lot of men did not take us seriously at first," admits Patricia. Now, she says, "They see we do know something." Then she exhibits some of the humor she has inherited from her father. "We're not just blonde."

The Perez-Carrillos — Life After La Gloria

It's not easy to walk away from one of the best-known cigar brands in the world. Moving into the arms of your children makes it easier. In March, 57-year-old Ernesto Perez-Carrillo left the La Gloria Cubana brand, the cigar that was the hottest cigar brand in America in the early 1990s. Perez-Carrillo left to work with his children, daughter Lissette, 35, and son Ernesto Perez-Carrillo III, 27.

"One of the main reasons I decided to leave is that my children want to get involved with the new company," Perez-Carrillo said at the time. "The opportunity to work with my kids is a once-in-a-lifetime opportunity."
His daughter worked as a lawyer, his son was a private equity executive with Kohlberg Kravis Roberts & Co., the famous leveraged buyout firm. They are "two of the people that I trust most in my life," said the elder Perez-Carrillo during a family lunch in late June. Though eight years separate his children, they could almost pass as twins with their jet-black hair and lean frames. Lissette has her father's intense, piercing dark eyes and both have inherited his distinctive jawline.

In the late 1970s, when La Gloria was largely unknown outside of the Little Havana neighborhood in Miami where it was rolled, young Lissette would watch her father work and sometimes lend a hand. "As a child I would go to the factory very often," she says. When she was five, six and seven, she would band cigars, and put them in cellophane. As a tween, she would work on customer lists, then later she went to trade shows. All that time spent in a cigar factory had an impact, imparting upon her a knowledge of Cuban slang that perplexed her friends. "These colloquial Spanish terms—my friends would say, 'How do you know that?'" she laughs.

In college, Lissette helped her father and mother with shipping
cigars, and took orders over the phone, particularly when a certain cigar magazine profiled La Gloria's then small operation in Miami, running a photograph of the family.
"It was surreal—the phones wouldn't stop ringing," she says.

When Ernesto Perez-Carrillo left his La Gloria Cubana brand in early 2009, he turned to his son Ernesto III and daughter Lissette for help in creating a new venture making E.P. Carillo cigars.

Like their father before them, Lissette and Ernesto III were encouraged to seek their own careers, not just join the family business. Their cigarmaker father tried a stint at drumming before dedicating himself to the cigar business, thumping the skins for several bands, including Tu Madré, and The Shadows (who once opened for KC and The Sunshine Band). "They were going to do their own thing," says Perez-Carrillo. "It's good to let kids go and do what they want, like when I wanted to be a drummer—now there's no looking back in regret."

Lissette went to law school, got married and had two children; Ernesto III began working in private equity and consulting. Each hoped to return to the La Gloria business. "I was the only one [in law school] who said my goal was to go back to Miami and run a cigar factory," says Lissette.

But the business had changed—production of La Glorias soared after 1995 when, to meet burgeoning demand, Perez-Carrillo began rolling cigars in the Dominican Republic on a scale six times larger than at his tiny Miami facility. Then the offers came rolling in. Ernesto Perez-
Carrillo fielded six serious offers for his El Credito Cigars Inc., and finally sold his company to Swedish Match AB (now the parent company of General Cigar) in 1999 for an estimated $40 million. Even though the numbers involved were life-changing he labored over the decision to sell (Perez-Carrillo had even turned down a larger offer).

"He tried to find every excuse not to do it," says Lissette. Admits her father: "It was hard for me to sell the business at first."

But Swedish Match didn't just want the brand—they wanted Perez-Carrillo to continue making it. Soon Swedish Match acquired General Cigar Co., the maker of Macanudos, and El Credito became a part of General. Having the much bigger company's sales force behind him helped move La Glorias at an unprecedented rate.

However, his being a part of a big company eventually chafed at Perez-Carrillo, and he yearned to do things on a smaller scale once again, this time with his family. His artistic creativity needed to be stirred.

"It's very exciting," says Ernesto Perez-Carrillo III. "It feels good to build something from scratch together. The whole family is really getting behind it…. We're all chipping in. We each have things to bring to the table." Ernesto III will focus on building the customer base, particularly in the New York area, where he lives. His sister will do all the legal work for the company, and is setting up the warehouse and offices in Miami, her home. "I'm going to be servicing all these orders Ernie's going to get," she says with a smile, giving her little brother some good-natured
ribbing. She also intends to set up a smoking lounge in the company headquarters, just minutes from historic Calle Ocho.

The elder Perez-Carrillo is focusing on cigars and the tobacco needed to make them, and his children know they have a long way to go before they can take up his blending reigns. "He's the cigar man," says his son. The father has embarked on a tobacco-buying spree. By late June, he had already bought tobacco from six farms in Nicaragua alone, and he was planning on buying more. "In October and September, we're going to go out and buy a lot more tobacco," he says, puffing on a prototype smoke.

The children won the first battle with their father, convincing him to move at an accelerated pace to get the business started. Perez-Carrillo originally didn't plan on having a cigar out until 2010, but the new plan has them on pace for a November or December 2009 launch. "The plan was to start in March or April [2010], set up the factory slowly, make
cigars for other people," Perez-Carrillo explains. "We're working on the factory now."

The brand will be their own, and will be called E.P. Carrillo. The first will be available in a limited-edition version (bearing a second band reading "Edición Inaugural 2009") and made with low-yield tobaccos. The core brand will come on the market later. "The plan is to do one limited edition per year," says Ernesto III.